DealQuest Podcast with Corey Kupfer

From closing dinner conversations that changed his career trajectory to advising on transactions up to half a billion dollars, Channing Hamlet shares proven strategies for selling businesses at premium valuations through proper preparation, understanding sector-specific value drivers, and creative deal structures. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Channing Hamlet, Managing Director at Objective Investment Banking and Valuation, who has over 30 years of experience advising business owners on management issues, transaction execution, and business valuation. Channing's firm specializes in lower middle market transactions, typically ranging from $10-25 million up to $100-150 million in value. WHAT YOU'LL LEARN: In this episode, you'll discover how buyer expectations have dramatically shifted over 25 years and why preparation requirements for premium valuations have intensified. Channing explains why clean accounting is no longer optional, how financial projections can make or break your valuation, and the three key value drivers beyond revenue and EBITDA. You'll also learn creative deal structures that can save transactions when traditional financing becomes challenging. CHANNING'S JOURNEY: Channing's path into dealmaking started at the family dinner table, where his father frequently hosted business visitors for dinner conversations about deals and transactions. His pivotal moment came while working at Legg Mason doing M&A, when a patriarch from a third-generation family business pulled him aside at a closing dinner and shared how much the work had changed his family's life. That moment hooked him on helping entrepreneurs and family businesses navigate successful exits. KEY INSIGHTS: In the mid-1990s, private equity firms paid four to six times EBITDA. Today, good companies sell for 10 to 14 times EBITDA, but buyers expect sellers to show up polished and prepared. Channing identifies three major value drivers beyond EBITDA. First, understanding what drives value in your specific sector. Second, building predictability through recurring revenue and systematized operations. Third, clearly articulating your differentiation and unique value proposition. Financial projections matter because selling takes approximately nine months, meaning buyers pay based on projected results, not historical performance. A last-minute budget won't stand up to scrutiny. Channing also shares a creative deal structure where seller financing at 10% interest saved a transaction when traditional bank financing fell through. Perfect for business owners considering an exit in the next 3-5 years, M&A advisors working with lower middle market companies, and anyone wanting to understand what truly drives premium valuations. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/channinghamlet FOR MORE ON CHANNING HAMLET: https://objectivecp.com https://www.linkedin.com/in/channing-hamlet/ FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [00:00] - Introduction: Channing Hamlet's journey from family dinner table conversations to investment banking [02:17] - Growing up around business deal discussions and choosing the outdoor life [03:45] - The closing dinner moment that changed everything at Legg Mason [08:19] - How the M&A landscape has transformed over 25 years [10:26] - Why buyer expectations and preparation requirements have increased   [18:52] - Understanding sector-specific value drivers through the printing industry example  [23:39] - Market outlook for 2023 and beyond [31:43] - The three legs of Objective's valuation practice[40:03] - Finding Objective Capital Partners and getting in touch Guest Bio Channing Hamlet is a Managing Director at Objective Investment Banking and Valuation, focused on leading the firm's valuation advisory service practice and transaction execution for its investment banking services practice. He is a results-driven executive with 30+ years of experience advising owners on management issues, transaction execution, and business valuation. Channing draws on a diverse background that includes direct management experience, strategy consulting, private equity investing, investment banking, and business appraisal experience to advise his clients. He is actively involved in the LA and San Diego business communities and has spoken at numerous organizations including EO. He was chosen as the Investment Banking Visionary for 2022 and 2021 in Banking and Finance magazine. Host Bio Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. Show Description Do you want your business to grow faster? The DealQuest Podcast with Corey Kupfer reveals how successful entrepreneurs and business leaders use strategic deals to accelerate growth. From large mergers and acquisitions to capital raising, joint ventures, strategic alliances, real estate deals, and more, this show discusses the full spectrum of deal-driven growth strategies. Get the confidence to pursue deals that will help your company scale faster. Related Episodes Episode 350 - Tom Dillon: When NOT to Take Venture Capital Money: Explore valuation considerations and preparing for exit from a fractional CFO perspective. Episode 330 - Pete Mohr: Building Exit-Ready Businesses: Discover how to build a business that commands premium multiples through systematization and predictability. Episode 332 - John Martinka: Exit with Style, Grace, and More Money: Learn practical strategies for maximizing value when selling your business. Episode 339 - Solocast 74: Exit and Succession Planning: Corey's insights on preparing for successful business transitions and the importance of advance planning. Episode 88 - Internal Succession Deals: Explore options for transitioning business ownership to next-generation leadership.   Keywords/Tags business valuation, selling a business, M&A preparation, EBITDA multiples, exit strategy, investment banking, lower middle market transactions, sell-side advisory, company valuation, premium valuation, buyer expectations, financial projections, value drivers, private equity, business sale preparation, transaction execution, family business sale, entrepreneurship, dealmaking, business growth strategies

From chief marketing officer at the first internet bank to building the leading annuity platform for RIAs, David Lau shares proven strategies for raising capital, navigating public company challenges, and why converting commission-based revenue to fee-based can multiply your exit value by five times. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with David Lau, founder and CEO of DPL Financial Partners, who has raised over $500 million across multiple ventures and built DPL into a platform serving more than 10,000 advisors at over 3,500 RIA firms. WHAT YOU'LL LEARN: In this episode, you'll discover why organic growth matters far more than market growth when acquirers evaluate your business, how converting commission-based annuity business to fee-based can multiply both your revenue and your exit multiple, the real tradeoffs of taking institutional capital and signing up for aggressive growth, the critical difference between venture capitalist optimism and private equity scrutiny, and how recognizing when your business has "run its course" can open the door to building something bigger. DAVID'S JOURNEY: David's career began as chief marketing officer of Telebank, the first internet bank, where he helped raise over $500 million. When preparing to go public, the stock jumped from $17 to $150 in weeks before Goldman Sachs stabilized pricing at $105. He later built Jefferson National, an insurance carrier he sold to Nationwide. That experience taught him the valuable part was distribution, not the capital-intensive balance sheet, leading directly to founding DPL in 2018. KEY INSIGHTS: A billionaire David met admitted he "mistook a bull market for brilliance." Acquirers only pay premium multiples for organic growth. If you did nothing different over the last decade as an RIA, you're making twice as much just from market performance. Buyers know this. Converting from commission to fee-based transforms exit potential with three times the revenue and five times the multiple, while expanding your buyer pool. DPL's technology reviews 2,500 policies per hour, and a significant portion of DPL's $4 billion in annuity sales were M&A related. When launching DPL, David planned to bootstrap until meeting Todd Boehly. Taking institutional capital means signing up for aggressive growth where some team members won't make it to the next stage. Venture capitalists are optimists who see your vision. Private equity investors see everything that can go wrong. Perfect for RIA owners considering M&A, hybrid advisors evaluating fee-based transitions, and entrepreneurs weighing capital raising decisions. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/davidlau FOR MORE ON DAVID LAU: https://www.dplfp.com https://www.linkedin.com/in/david-lau-b6449b7/ https://x.com/dpl_fp FOR MORE ON COREY KUPFER: https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [00:00] - Introduction: David Lau's journey to building DPL Financial Partners [04:00] - Capital raising at Telebank: $500 million raised, stock jumping from $17 to $150 [08:00] - The tradeoffs of taking institutional capital and signing up for aggressive growth [12:00] - Venture capitalists as optimists versus private equity investors who see downside [16:00] - Why choosing the right capital partners matters more than just getting funded [20:00] - How DPL solved the RIA insurance problem with commission-free products [24:00] - Converting to fee-based: Three times the revenue and five times the multiple [28:00] - Why organic growth matters more than market growth in valuations [33:00] - The future of RIA consolidation and when to sell a business [40:00] - Freedom: Working with Russian defectors and gaining perspective Guest Bio David Lau is founder and CEO of DPL Financial Partners, the leading annuity platform for RIAs. Since 2018, DPL has worked with 20 insurance carriers and built an advisor base of more than 10,000 advisors from over 3,500 RIA firms. Before founding DPL, David was COO of Jefferson National, which he helped build and sell to Nationwide. Earlier, he served as chief marketing officer at Telebank, the first internet bank, where he helped raise over $500 million. His work has been covered in The Wall Street Journal, The New York Times, Barron's, and CNBC. DPL is backed by Todd Boehly's Eldridge and Bob Diamond's Atlas Merchant Capital. Host Bio Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. Show Description Do you want your business to grow faster? The DealQuest Podcast with Corey Kupfer reveals how successful entrepreneurs and business leaders use strategic deals to accelerate growth. From large mergers and acquisitions to capital raising, joint ventures, strategic alliances, real estate deals, and more, this show discusses the full spectrum of deal-driven growth strategies. Get the confidence to pursue deals that will help your company scale faster. Related Episodes Episode 350 - When NOT to Take Venture Capital with Tom Dillon: Explore alternative funding sources when traditional VC doesn't fit your exit strategy. Episode 339 - Next-Gen Leadership and M&A: Why G2 Matters: Understand why developing Generation 2 leadership commands premium valuations. Episode 209 - M&A Talk with Leading RIA Aggregators and Integrators: Bob Oros of Hightower Advisors: Explore what aggregators look for in acquisition targets.   Keywords/Tags s RIA M&A, capital raising, fee-based revenue, commission-free annuities, DPL Financial Partners, organic growth, enterprise value, hybrid advisor transition, RIA consolidation, private equity, venture capital, going public, IPO, exit strategy, insurance for RIAs, annuity platform, wealth management M&A, financial services, startup funding, institutional capital, valuation multiples, deal structures, business growth strategies, dealmaking

What if losing your life savings on your first investment at age 27 became the catalyst for understanding why 90% of startups get stuck for the same psychological reasons? That's exactly what happened to Dave Hersh, founding CEO of Jive, board partner at Andreessen Horowitz, and author of Reignition. Dave grew Jive from an open-source project to a NASDAQ IPO, bootstrapping to $12 million over five years before raising venture capital. But when he watched Atlassian, a comparison company that started at the same time, stay on their original trajectory and become worth over $20 billion while Jive eventually died on the public markets, he realized fear and insecurity had driven his capital decision rather than genuine strategy. That painful lesson shaped everything Dave now teaches as an executive coach and General Partner at Metamorph Partners. After working with hundreds of stuck companies, he discovered that 90% of failures trace back to the same psychological patterns. Not cash. Not product market fit. Not competition. Subconscious patterns driving decisions without founders knowing. The statistics are sobering. Between 80 to 95% of founders suffer mental health issues while running their companies. Even successful founders have an 85% chance of experiencing depression or struggles for up to 10 years post-exit. Only 15% are truly thriving after they sell. Dave introduces his inner board meeting framework, which helps founders identify the internal parts driving major decisions. The child wanting safety. The hero wanting to save everyone. The warrior that cannot let go. When you understand these patterns, you can work toward compromises that break through stalemates. The conversation covers when and why to raise capital versus bootstrap, the transition process between identities that most founders skip, and the human-first competitive moats that will define success in the AI era. For founders navigating capital decisions, stuck companies, or the complex terrain after exit, this episode offers a different lens on what actually determines outcomes. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/davehersh FOR MORE ON DAVE HERSH:https://www.linkedin.com/in/davehersh/https://one-in-ten-thousand.beehiiv.com/  FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [00:00] - Introduction: Dave Hersh's journey from dot-com era to executive coaching [02:30] - Growing up in Newport, Rhode Island with no entrepreneurial modeling [05:15] - First entrepreneurial experience: selling ninja weapons to neighborhood kids [07:45] - Arriving in New York on September 10th, 2001 and founding Jive [12:00] - Bootstrapping to $12 million over five years without outside capital [16:30] - The Facebook moment and decision to raise venture capital in 2006 [21:00] - Why founders equate raising money with success and the 10% reality [25:45] - The Atlassian comparison and what could have been a $20 billion outcome [30:15] - Mental health statistics: 80-95% of founders suffer while running companies [34:00] - Post-exit malaise: 85% of successful founders struggle for up to 10 years [43:00] - Identifying internal parts: the child, hero, warrior, and insecure parts [51:30] - Human-first moats in the AI era Guest Bio Dave Hersh is an executive coach, speaker, and investor based in San Francisco with over 30 years of experience in strategy, startups, and conscious leadership. He was the founding CEO of Jive, which he grew from an open-source project to a NASDAQ IPO. He also spent two years as a Board Partner (investor) at the venture capital firm Andreessen Horowitz. He is the author of Reignition, a playbook for helping startups get unstuck and find their breakthrough, and is working on a new book about enlightened leadership in the era of AI. Dave currently serves as General Partner at Metamorph Partners. Host Bio Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. Show Description Do you want your business to grow faster? The DealQuest Podcast with Corey Kupfer reveals how successful entrepreneurs and business leaders use strategic deals to accelerate growth. From large mergers and acquisitions to capital raising, joint ventures, strategic alliances, real estate deals, and more, this show discusses the full spectrum of deal-driven growth strategies. Get the confidence to pursue deals that will help your company scale faster. Related Episodes Episode 366 - Jodi Hume: Founder Exits and the Emotional Journey Behind Major Business Decisions: Explore the psychological dimensions of exits and what founders need to prepare for beyond the transaction. Episode 350 - Tom Dillon: When NOT to Take Venture Capital Money: Discover alternative funding sources and how to evaluate whether VC is right for your business model. Episode 302 - Laurie Barkman: Preparing for a Successful Exit with Business Transition Insights: Learn the practical steps for getting your business exit-ready. Episode 328 - Richard Manders: Post-Exit Transitions and Finding Purpose After Selling Your Company: Understand how successful founders navigate identity after major exits. Social Media Follow DealQuest Podcast:LinkedIn: https://www.linkedin.com/in/coreykupfer/Website: https://www.coreykupfer.com/ Follow Dave HershLinkedIn: https://www.linkedin.com/in/davehersh/ Newsletter: https://one-in-ten-thousand.beehiiv.com/ Keywords/Tags founder mental health, post-exit depression, startup psychology, venture capital decision, inner work for CEOs, executive coaching entrepreneurs, identity after exit, bootstrap versus venture capital, founder burnout, stuck companies, inner board meeting, conscious leadership, Jive Software, Andreessen Horowitz, Reignition book, founder transitions, ego in business, capital raising psychology, entrepreneurial mental health, exit preparation, business identity, human-first leadership, AI era leadership

From jumping straight to deal structure to building repeatable acquisition programs that scale, Corey Kupfer shares the exact whiteboarding process he uses with clients to create successful deal programs across M&A, joint ventures, licensing, and any deal-driven growth strategy. In this solocast episode of the DealQuest Podcast, host Corey Kupfer walks through the five critical steps that must come before deal structure when building a repeatable deal program. Drawing on 35+ years of deal-making experience and countless whiteboarding sessions that have helped create platforms completing dozens of transactions, Corey reveals why most attorneys start in the wrong place and how proper planning separates successful programs from expensive mistakes. WHAT YOU'LL LEARN: In this episode, you'll discover why deal structure should be the sixth step in your process, not the first, and how to identify your personal and business motivations before pursuing any deal program. Corey shares the five whys technique from Honda's former CEO to uncover your real drivers, how to define your ideal target or partner profile to avoid wasting time on opportunities that don't fit your strategic criteria, and why your value proposition must differentiate you from competitors who may have more capital. You'll learn how to assemble the right deal team with both internal and external expertise, why building a repeatable model before doing individual deals prevents cap table nightmares and integration problems, and the power of having template documents ready to demonstrate you're a serious player. The framework applies whether you're pursuing acquisitions, joint ventures, licensing deals, franchising, or any other deal-driven growth approach. THE WHITEBOARDING PROCESS: Most clients come to Corey asking about deal structure. What should the terms be? Should they pay cash or offer equity? What about earnouts? These are important questions, but they're not where you should start. After doing whiteboarding sessions with countless clients over 35 years, Corey can say with complete confidence that every single one has gotten significant value from the process. The firms that skip these steps end up with inconsistent deal structures, cap table problems, and integration nightmares. The companies that do this right create efficient, repeatable processes that let them scale their deal programs. THE INTERNAL JOURNEY: Corey often talks about things other lawyers don't discuss. He focuses on the internal journey, making sure business leaders and executives move forward on deals from the right place. When you get to wherever you think you want to go, you should actually be happy and satisfied, and it should help you achieve your objectives and goals. Too many entrepreneurs pursue growth strategies based on external pressures or assumptions about what they think they should be doing, based on entrepreneurial wisdom out there. They grow and do things in ways that don't actually end up making them happy and satisfied and aren't necessarily best for their business. STEP ONE: START WITH YOUR WHY: The first question in every whiteboarding session is why. Not just the corporate why, although that matters. Corey wants to know your personal why as the founder or executive driving this strategy. If your why is geographic expansion because your clients need services in other markets, that's legitimate. If your why is adding capabilities that will create a better integrated client experience, that works too. If your why is increasing enterprise value before an exit in five or ten years, there's no judgment about that. You just need to be clear on what drives you, because that clarity will shape every subsequent decision. Corey uses the five whys technique, which comes from the former CEO or chairman of Honda. You ask why five times, going deeper with each question. Why do you want to grow? To get bigger. Why do you want to get bigger? To serve clients better. Why will that serve clients better? Because they have needs we currently send elsewhere, and integration would improve their experience. Why does that matter to you? Because I genuinely care about my clients and believe this will make them happier while helping our company grow. That depth of understanding separates deal programs that succeed from those that become expensive distractions. STEP TWO: DEFINE YOUR TARGET PROFILE: Once you know your why, you can determine who you should be targeting. This is where many firms waste tremendous time and energy. Doing deals is a distraction from running your business, especially if you don't have a dedicated corporate development team with finance people, legal resources, and integration specialists. You need to be surgical about who you pursue. Think about the wealth management space, which Corey works in extensively. There are huge numbers of buyers right now. The market is incredibly competitive. If you're trying to compete with private equity backed aggregators on their terms, you'll lose every time. They can pay top dollar, close fast, and offer the second bite of the apple through rollover equity and multiple arbitrage. If you don't have PE backing, you need a completely different value proposition. Maybe it's culture. Maybe it's the opportunity for advisors to expand their service offerings. Maybe it's taking administrative burden off retiring founders so they can focus on what they love. Your value proposition should be authentic to who you are and what you can actually deliver. STEP THREE: ASSEMBLE YOUR DEAL TEAM: Before you start actively pursuing deals, you need to know who will be on your deal team, both internally and externally. This includes whoever sources deals for you, whether that's an internal corporate development person, an investment banker, a recruiter, or a consultant. You need financial expertise, and it better be someone with deal experience. Accountants, CFOs, and controllers who have never worked on transactions are very different from those who have. The same goes for legal. Your general corporate lawyer is not the person to build your deal program. Then you have all the integration functions. Technology integration. HR and culture integration. Client communication and retention strategies. You might not have every person in place on day one, but you need to know what roles are required and have a plan for filling them before you close your first deal. STEP FOUR: BUILD YOUR MODEL: This is where most companies make a critical mistake. They do deals opportunistically without creating a consistent model first. Someone approaches them, they negotiate terms, they close. Then another opportunity comes along, they do it differently. After three or four deals, they have completely different structures with different equity classes, different earnout provisions, different everything. This creates massive problems. If you have different classes of equity, your cap table becomes a mess. If sellers talk to each other and realize they got very different deals, you have credibility issues and potential legal exposure. Integration becomes nearly impossible because you don't have standardized processes. The best acquirers find their model and make it repeatable. They have template legal documents. They have standardized financial analysis and underwriting processes. They have systems for due diligence and integration. Every deal follows the same fundamental structure with minor variations based on specific circumstances. When you build your model, you're deciding the big conceptual components. Are you doing all cash deals or creating an equity class for rollover? How much will you pay upfront versus over time? Will you have retention requirements tied to revenue or client retention? What about earnouts for partners who stay involved in growth? In service businesses where client relationships matter, you almost always want some backend money contingent on retention. If you're buying a manufacturing business with hard assets, the calculus is different. STEP FIVE: DRILL DOWN TO DEAL STRUCTURE: Once you have your model, you can determine the actual deal structure for individual transactions. What specific equity class will you offer? If you're an S corp, you can only have one class of equity. Will you restructure as a C corp or an LLC to offer different equity terms? What exact percentage will you pay upfront versus backend? Over how many years? If you know you're targeting retiring business owners who want to cash out, they probably want more money upfront and less backend risk. If you're targeting younger partners who want to stay and grow, they might prefer less upfront and more backend upside. All of these specific terms fit within your broader model. You're not reinventing the structure for each deal. You're applying your established approach with minor customizations based on the specific situation. THE POWER OF TEMPLATE DOCUMENTS: The ideal scenario is completing your whiteboarding session, building your model, and creating template legal documents before you start seriously pursuing targets. When someone expresses interest, you can immediately send a letter of intent. You can start due diligence with established processes. You can deliver definitive legal documents quickly. This makes you look professional and serious. It shows potential partners that you know what you are doing and have your act together. Speed matters in competitive markets. Corey understands the practical reality. Template documents cost legal fees before you have a deal in place. Some clients aren't willing to make that investment without more certainty. Others have already started conversations with potential partners before they come in for the whiteboarding session. Recently, a client did the whiteboarding session in the morning, then met with a potential seller that same afternoon. The seller was ready to move faster than expected. The documents got built for that specific dea

From losing his $25,000 life savings on his first startup investment to democratizing venture capital for everyday investors, Gerry Hays shares proven strategies for making early-stage investing accessible through VentureStaking while teaching founders outside traditional tech hubs how to raise capital and build sustainable businesses. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Gerry Hays, founder and CEO of Doriot and Senior Lecturer at Indiana University's Kelley School of Business. Gerry has made 75+ startup investments, taught venture capital for 20 years, and built multiple companies from zero to exit, including HomeYeah.com and Charlie Biggs Food Company. His current mission focuses on expanding venture capital access beyond coastal hubs through innovative funding models. WHAT YOU'LL LEARN: In this episode, you'll discover how to participate in early-stage startup investing with as little as $10 through the VentureStaking model, why the right to invest later in winning companies proves more valuable than over-investing today, and how collapsing startup costs are fundamentally changing capital requirements for founders. Gerry shares strategies for avoiding what he calls "the fool's tax" when making your first investments, the critical importance of backing founders over ideas, and why venture investing resembles poker more than roulette. You'll also learn about building venture ecosystems within universities where students and alumni can collaborate on funding and growth, navigating the decision between raising capital versus bootstrapping your business, and the difference between venture-appropriate businesses versus lifestyle companies. The conversation explores tokenization's potential to create an ownership economy, why cultivation mindset beats consumption thinking for long-term wealth building, and what freedom from scarcity truly means in both dealmaking and life. GERRY'S JOURNEY: Gerry's path into venture capital came through painful education. After leaving law practice after just six months, he made his first investment at age 27, putting his entire life savings of $25,000 into a hazardous waste processing technology. He knew the space intimately from running lobbying for Indiana's Department of Environmental Management. The technology made sense. The market opportunity was clear. But the founder couldn't execute, and Gerry lost everything. That lesson kept him away from startup investing for a decade. Instead, he became a founder himself, launching HomeYeah.com during the dot-com boom. He acquired a small Indianapolis company with 25 lawn signs and built it into the 11th largest real estate company in Indianapolis by transactions, growing from zero to $1.8 million in revenue in just 20 to 24 months. The company sold to Help-U-Sell Real Estate in 2003, but not before Gerry experienced the challenge of raising capital outside traditional tech hubs. After the HomeYeah.com exit, Indiana University invited him to teach a new venture capital course. He's been there since 2004, creating what he calls a bridge between academic theory and real-world startup practice. Meanwhile, he co-founded Charlie Biggs Food Company, scaling it from zero to $10 million in revenue with distribution in over 1,000 retail locations before exiting through a private equity deal. FIRST INVESTMENT LESSONS: That initial $25,000 loss taught Gerry what he calls "avoiding the fool's tax." The fundamental insight was simple but profound. When you invest, you're really investing in founders more than ideas. He was simply a bad picker of founders at that point. The technology expertise didn't matter. Market knowledge didn't matter. What mattered was identifying founders who could execute through inevitable obstacles and pivots. This lesson shaped everything that followed. Gerry wouldn't touch startup investing again for ten years after that loss. When he did return, his approach centered on cultivating relationships with founders over time, watching how they respond to challenges, and building diversified portfolios that acknowledge most investments will fail. VENTURESTAKING MODEL: The VentureStaking approach emerged from Gerry's years of teaching and investing. The model allows investors to participate with as little as $10 in early-stage founders. Instead of writing large checks for immediate equity, venture stakers provide small grants to founders just getting started. If those founders break out and raise a real equity round, the stakers get invited to invest at 10 times their initial stake. The math works elegantly. Out of 25 investments of $10 each totaling $250, you might only see three worth backing in a real round. But when winners emerge, you've earned the right to participate in meaningful equity rounds without the traditional barriers to entry. This democratizes access while maintaining sophisticated portfolio construction principles. Gerry likens venture investing to poker rather than roulette. You play many hands with small amounts. You fold most of them. But when you spot real winners, you bet heavy. This is cultivation versus consumption, a long-term wealth-building game that Warren Buffett exemplifies, having created 99% of his wealth after age 65. THE COLLAPSING COST OF STARTING: One of the most profound shifts Gerry identifies is how startup costs have collapsed. What required $5 million to build ten years ago can now be created in a day for $50 thanks to AI agents, no-code platforms, and cloud services. This changes everything about capital requirements and who can be a founder. This trend combines with tokenization to create what Gerry calls an ownership economy. Instead of owning a few stocks generating passive income, people could hold tokens in 150 companies, each generating small amounts of passive income without traditional barriers to entry. The infrastructure for this future is being built now through blockchain technology and regulatory evolution. UNIVERSITY VENTURE ECOSYSTEMS: Gerry's work brings the VentureStaking model to universities, creating ecosystems where students, alumni, and faculty can participate in funding and building the next generation of startups. Indiana University has 70,000 students and 800,000 alumni. Imagine creating an arena where students pitch ideas, alumni back them with small stakes, and the community participates in the upside when founders succeed. Shared information, shared risk, shared prosperity. This approach captures innovation traditional VCs miss entirely. Founders outside coastal hubs gain access to capital. Alumni gain access to investment opportunities typically reserved for accredited investors with six-figure minimums. Students learn by doing rather than just studying theory. The model scales to any university willing to build the infrastructure. KEY INSIGHTS: Geographic location shouldn't determine access to capital. Gerry experienced this firsthand with HomeYeah.com in Indianapolis. He wasn't in California. He didn't have the right connections. That challenge drives his current work at Doriot, focused on democratizing venture capital for founders and investors outside traditional hubs. The Sam Altman example illustrates how network effects compound. Altman invested $15,000 in Stripe in 2009, now worth $650 million. That wealth creates access to more deals. Those deals create more wealth. The rich get richer not because they're smarter but because they have access. VentureStaking aims to expand that access. Contracts matter, but people matter just as much. Gerry's experience shows that when something seems too easy, like tenants responding unusually quickly to lease documents without redlines for 10-15 year commitments, it raises red flags. You can have perfect legal documents but still face challenges if you're working with the wrong people. THE SHARK TANK STORY: Gerry shares his Shark Tank experience where his former student pitched a business and received a $250,000 offer from Mark Cuban for 35% equity. Gerry advised him that existing SAFEs would push him below 50% ownership. The founder turned down Cuban's offer. That "no" to Mark Cuban kicked off Season 4 of Shark Tank and generated publicity that proved more valuable than the deal itself. The company continued growing without the investment. CULTIVATION VERSUS CONSUMPTION: One of Gerry's most powerful insights addresses how society trains people for consumption rather than cultivation. We've made sports betting legal. Prediction markets are booming. We're training young people about fast-moving money and dopamine hits. But venture investing is a cultivation game. You're dropping seeds into the ground and watching what the universe brings back. He gave a student $5,000 who wanted to build something in the travel industry. The founder pivoted to AI and Shopify and just raised $8 million at a $55 million valuation. That $5,000 investment is now worth over $200,000. The bet wasn't on the idea. It was on a founder who wouldn't quit. That's something you discover by playing the game, getting yourself into wealth-building activities where you're patient, watching, and learning. FREEDOM FROM SCARCITY: When asked about freedom, Gerry's answer cut to something fundamental. Being free from a scarcity mindset is profoundly important. Everything around us reinforces scarcity. But when you let go of that and realize how abundant things really are, it changes how you see opportunities. You can afford to be patient. You can take calculated risks. You can help others succeed knowing there's enough to go around. This mindset applies to venture capital, to dealmaking, to entrepreneurship, and to life. When you operate from abundance rather than scarcity, you see opportunities differently. Capital formation is evolving. The question is whether that evolution will democratize opportunity or concentrate it further. Gerry's betting on democratization. Perfect for investors curious about venture c

From professional wakeboarder to CEO managing $250M+ in commercial real estate investments, Nick Jones shares proven strategies for building successful real estate businesses through strategic partnerships, effective capital raising, and protecting investor interests. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Nick Jones, CEO of Alakai Capital, who has underwritten and acquired over 70 commercial investments and developments representing more than $250 million in value. Nick currently oversees 800,000+ square feet of industrial, retail, office, and medical assets across multiple states. WHAT YOU'LL LEARN: In this episode, you'll discover how to raise outside capital for your first commercial real estate deal while protecting downside risk, why syndication can work better than funds when you can close deals quickly with trusted investors, and the surprising truth about "off-market" deals versus listed properties in today's transparent market. Nick shares how to build broker relationships that generate consistent deal flow without constantly hunting for opportunities, due diligence strategies when high-credit tenants won't share financial information, and why Covid flipped conventional wisdom about credit tenants versus mom and pop operators. You'll also learn about the strategic value of balancing consistent real estate returns with selective angel investments, how to navigate market trends including drive-through retail and efficiency-focused opportunities, and what freedom means beyond just financial independence. NICK'S JOURNEY: Nick's path wasn't linear. Growing up near Microsoft and Nintendo in Redmond, Washington, he found real estate "incredibly boring" until witnessing how it connected to fascinating industries. After his father and grandfather passed away during his senior year of high school, Nick moved to Florida to pursue professional wakeboarding, eventually earning a podium finish at the World Championships in 2011 while graduating summa cum laude from the University of Central Florida. The dean of UCF's real estate program, whose son was also a professional athlete, reignited Nick's interest in commercial real estate investment and development. Nick started in land brokerage during 2011-2012 when Florida land was worth less than the buildings next to it, learning through challenging cold calls to developers. FIRST DEAL LESSONS: Nick's entry into investing came through a vacant Taco Bell property. Working with a broker partner, they secured the building, signed a 10-year lease with a new tenant, and only had to replace the HVAC and roof. The timing proved fortunate - securing 80% loan to value at 2% interest on an interest-only basis during the post-financial crisis recovery. That first deal taught valuable lessons about protecting downside risk and building tenant relationships while delivering one of his strongest returns ever. CAPITAL RAISING EVOLUTION: For his first capital raise, Nick bought an old bank branch all cash with plans to tear it down and build a quick service restaurant. To protect downside risk as a new sponsor, he structured it with no debt and two years of interest and tax reserves. After approaching friends' parents, fellow brokers, and creating a detailed investment memorandum, a tenant approached wanting to lease the existing building as-is with a 10-year lease. Nick refinanced at 50% LTV, pulled equity out, and used those proceeds to buy a second deal. That snowball effect has grown to approximately 100 investors making about 500 investments with his company. KEY INSIGHTS: Nick continues syndicating individual deals instead of raising funds because his deals follow similar patterns with consistent return theses. This approach gives investors freedom to select which markets and property types align with their preferences while maintaining speed to close. Managing investor capital creates heightened responsibility that sharpens every aspect of deal execution. Nick approaches it similarly to personally guaranteeing loans - while losing your own capital is unfortunate, losing someone else's carries profound implications for relationships and reputation. The biggest lesson from deals that didn't go as planned: contracts matter, but people matter just as much. When tenants respond unusually quickly to lease documents without redlines for 10-15 year commitments, it raises red flags. During Covid, high-credit tenants had attorneys advising them to stop paying rent while small bay industrial mom and pop tenants maintained perfect payment records. BROKER RELATIONSHIPS: The majority of Nick's deals come through brokers he's built long-term relationships with over years. These relationships prove valuable because brokers trust Nick will maintain confidentiality, move quickly through underwriting, and they understand his investment criteria. After years of exchanging deals and feedback, brokers know which opportunities match his thesis. MARKET TRENDS: Interest rate movements create near-term positivity while inflation continues hitting sectors unevenly, creating inefficiencies and opportunities. The retail apocalypse predictions following Covid haven't materialized because people still crave experiences. Drive-throughs represent a clear trend as efficiency becomes paramount - almost every concept has figured out how to use them successfully, including Chipotle proving the model works for food types that seemed ill-suited initially. Perfect for real estate investors considering raising outside capital, operators building broker networks, and anyone interested in how successful commercial real estate investors structure deals and protect investor capital.FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/nickjones FOR MORE ON NICK JONES:https://www.alakai-capital.comhttps://www.linkedin.com/company/alakaicapital/https://www.linkedin.com/in/nickjonesrealestate/https://www.instagram.com/alakaicapital/ FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!   Episode Highlights with Timestamps [00:00] - Introduction: Nick Jones' journey from professional wakeboarder to real estate CEO [02:21] - Growing up around real estate near Microsoft and Nintendo in Redmond, Washington [04:21] - Pivoting from professional sports to commercial real estate after family tragedy [06:09] - The first deal: A vacant Taco Bell property that set the foundation [07:44] - Why Nick started with commercial properties instead of residential real estate [09:17] - Evolution of financing and capital raising strategies across 70+ deals [11:44] - Syndication vs funds: Why individual deal syndication works better [13:26] - The decision to raise outside capital and the weight of investor responsibility [14:15] - How grandfather and father approached real estate differently without raising capital [16:15] - Learning from deals that didn't go as planned: Contracts and people both matter [19:05] - Due diligence challenges with high-credit tenants who won't share financials [20:23] - Covid revelation: Mom and pop tenants paid while credit tenants had attorneys advise stopping rent [22:28] - How to source properties and build broker relationships that generate deal flow [25:52] - The truth about "off-market" deals in today's transparent commercial real estate market [27:59] - Balancing commercial real estate with selective angel investing for asymmetric returns [31:09] - Relying on specialized partners for angel investing due diligence [34:10] - Current market trends: Interest rates, inflation, drive-through retail, and efficiency plays [37:52] - Whether Nick's investor pool is set and how new investors can learn more [40:00] - What freedom means beyond financial independence: Physical, mental, and relationship dimensions [41:22] - The danger of gaining financial freedom while losing physical health or relationships [42:25] - Corey's "ideal life now" philosophy versus waiting for retirement Guest Bio Nick Jones has been involved in commercial real estate management, investment, development, and brokerage for over 20 years. Each role has added valuable perspective, introducing various angles and strategies to evaluate every opportunity Alakai Capital pursues. Currently, he serves as CEO managing acquisitions, development, and capital markets. Throughout his career, Nick has underwritten and acquired over 70 commercial investments and developments representing more than $250 million in value. He currently oversees 800,000+ square feet of industrial, retail, office, and medical office assets. Nick graduated summa cum laude from the University of Central Florida while simultaneously competing on the World Tour as a professional wakeboarder, earning a podium finish at the World Championships in 2011. He is an active member of ULI, ICSC, and NAIOP. Host Bio Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. Show Description Do you want your business to grow faster? The DealQuest Podcast with Corey Kup

Think making money and making impact are mutually exclusive? THINK AGAIN. Bob Bush went from working on the RJR Nabisco LBO to advising Dubai's government to co-founding a coffee company with NBA legend Dikembe Mutombo. His approach? Commerce, not charity. After 30+ years structuring deals across Wall Street, Africa, and the Middle East, Bob discovered that sustainable social impact requires sustainable economics. Now he's disrupting coffee supply chains where farmers get just 6 cents of your $5 latte. Key Takeaways: Why crossing cultural bridges creates the best deal opportunities How to build "shock absorbers" into social enterprises The power of democratizing investment through crowdfunding Why alignment beats optimization in building meaningful businesses Tune in to this episode to hear Bob Bush share his journey from Wall Street to creating social impact businesses across continents. From his insights on the RJR Nabisco deal to building sustainable supply chains in Africa, this conversation offers invaluable perspectives for business leaders seeking to create both financial value and social impact. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/bobbush FOR MORE ON BOB BUSH:https://www.linkedin.com/in/robertcbushjr/https://www.instagram.com/mutombocoffee/?hl=en FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!

Just wrapped my second year chairing the EO Deal Exchange Conference, and the lessons were off the charts. Here's what happens when you put hundreds of entrepreneurs in a room focused on one thing: growing through deals. Three insights that stood out: The wisdom is already in the room. We ran deal speed networking sessions where members shared their specific needs (buying companies, seeking JV partners, raising capital). The collective knowledge and connections in that room solved problems in minutes that could take months to crack alone. Stop looking outside your network for every answer. Exit satisfaction is shockingly low. Dave Hirsch shared that only about 13% of entrepreneurs who successfully exit are actually happy afterward. His "Inner Board Meeting" concept helps you identify all the different voices and aspects of your personality that need to be satisfied by any deal you pursue. Powerful framework for avoiding founder depression. Lifestyle business isn't an insult. Silicon Valley prodigy Fallon Fatemi, who co-founded an AI company with Mark Cuban, shared that she'll never raise capital again. Not because capital is bad, but because her priorities have shifted. Build the business and life YOU want, not what others expect.• • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/kraftheinz• • •FOR MORE ON COREY KUPFER:https://www.linkedin.com/in/coreykupfer/http://coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!

85% of founders have regrets about their exits. The research is clear. But here's what surprised me most about this statistic: almost none of them regret leaving money on the table. They regret the clarity work they didn't do beforehand. In my latest conversation with Jodi Hume, an advisor who works exclusively with founders and CEOs navigating acquisitions and exits, we explored what that clarity actually looks like: How to distinguish between what you can compromise on and what will keep you awake at night years later. Why energy management during due diligence directly impacts the quality of your decision-making. The identity piece nobody talks about: who you are after the company is no longer yours. How to protect yourself from making decisions born of depletion rather than strategy. The uncomfortable truth about founder burnout and when an exit might be the right call precisely because you've hit your limit. Jodi's approach is unusual. She's less interested in maximizing valuations than in ensuring founders actually get what they came for—and that they don't regret it afterward. Listen to the full episode if you're even thinking about an exit in the next few years. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/jodihume FOR MORE ON JODI HUME:https://www.linkedin.com/in/joditurnerhume/https://atthecore.com/ FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!

Concentration beats diversification. One stock. That's all Jaden Sterling bought during the 1990s. It tripled, became capital for 125 real estate deals, and eventually funded Sterling Stock Picker, a stock-picking platform now serving 3,000 investors. What most financial advisors don't tell you: diversification is what you do when you don't know what you're doing. When Jaden's clients at Merrill Lynch held 4-6 solid companies, they were pressured to sell and diversify into mutual funds. The math later showed holding those original positions would've beaten all the churn. The path to real wealth isn't about spreading money thin. It's about focused conviction in what you actually understand. I sat down with Jaden to talk about deal structures across real estate, concentrated stock investing, raising capital from customers instead of VCs, and why your relationship with money mirrors your relationship with yourself. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/jadensterling FOR MORE ON JADEN STERLING:https://www.sterlingstockpicker.com/jaden_sterling FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!

I just had an incredible conversation with Jon Wells on the DealQuest Podcast about a real estate niche that most investors have never even considered. After 25 years in Denver real estate, Jon discovered something remarkable: group homes for mental health and sobriety programs that generate 6%+ cap rates with almost zero landlord responsibilities. Here's what struck me most from our discussion: Jon's "fix and flop" philosophy completely changed my perspective. "My best deals were the ones that didn't sell," he told me. Those failed flips that he couldn't unload? They became his most profitable long-term holdings and led him to this overlooked niche. The economics are compelling. While everyone fights over compressed margins in traditional real estate (Jon watched fix-and-flip profits shrink from 25% to barely 10%), group homes maintain 6-13% cap rates even in high interest rate environments. His mentor has accumulated 1,000 beds. Jon manages 30-40 beds that provide what he calls "a great living." The structure is brilliantly simple. Operators funded by Medicaid and grants handle everything - maintenance, tenants, daily management. Property owners collect rent. It's "as close to a triple net deal as you can do" in residential real estate. The vetting process Jon shared was eye-opening. Drawing from his 1990s experience helping people save properties from foreclosure, he applies rigorous financial analysis to operators. The key: finding those with grant funding, solid track records, and willingness to accept purchase options so they treat the property like their own. What impressed me most was Jon's disciplined approach to avoiding shiny object syndrome. After a syndication advisor told him "I wouldn't touch that with a ten foot pole," he pivoted back to what he knows works - paying off mortgages and creating owner-carry notes for stable, predictable income. The lesson? While everyone chases the same crowded strategies, the best opportunities often hide in markets others don't even know exist. Sometimes the path to financial freedom isn't about following the crowd, but about finding overlooked niches that match your values and expertise. Listen to our full conversation on the DealQuest Podcast where Jon reveals his complete framework for evaluating group home opportunities. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/jonwells FOR MORE ON JON WELLS:https://www.linkedin.com/in/jonwellsrealtor/ https://abetterwayrealty.com/  FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!

Warren Buffett called it one of his biggest investment mistakes.The 2015 Kraft Heinz merger destroyed $63 billion in shareholder value while the broader market doubled.Key lessons for M&A professionals:• Consumer behavior trend analysis is critical for food industry due diligence • Aggressive cost reduction can eliminate innovation capacity in consumer products • Post-merger integration strategies must balance efficiency with brand development • Market research capabilities become essential during rapid cultural shifts • Strategic exit planning requires objective assessment of recovery prospectsThe complete merger failure analysis reveals why sophisticated investors missed consumer preference shifts toward natural foods and how 3G Capital's cost optimization strategy backfired in processed food markets.Essential listening for dealmakers in consumer products industries.• • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/kraftheinz• • •FOR MORE ON COREY KUPFER:https://www.linkedin.com/in/coreykupfer/http://coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!

Think great communication in deals is about having the right words or perfect hand gestures? After 35 years of negotiating deals, I can tell you this: all the tactical training in the world won't help if you haven't done the internal work to understand who you are and what you bring to the table. In this episode, Dia Bondi breaks down why your leadership voice matters more than any communication skill. She turned a $30,000 project into over a million dollars by structuring it as a mix of cash and equity. She helped a client maneuver a complex secondary deal by crafting a multi-layered ask that positioned him as an equal partner. And she showed a founder how to create $10 million in value by painting a picture that helped an entire room recognize the moment they were in. Dia shares her six attributes of clutch communicators, including how to:Make strategic asks that create value for everyone (not just get you what you want)Use killer setups that feel natural to your voiceBridge your unique perspective to whatever you're buildingShow up big in big moments even when it feels uncomfortable This conversation reveals why "be authentic" is useless advice and what to focus on instead. Perfect for founders heading into funding rounds, executives negotiating partnerships, or anyone who needs to speak powerfully when stakes are high.• • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/diabondi• • •FOR MORE ON DIA BONDILinkedIn: https://www.linkedin.com/in/dia-bondi/Company: https://www.diabondi.com/The Book: https://www.asklikeanauctioneer.com/FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/https://www.coreykupfer.com/Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!

"Every time I get off the phone with you, I feel better... but I don't call because I don't want to pay the billable hour."Alexandria Seydel heard this from clients constantly when she was practicing M&A law. So she made a simple offer: "What about once a month you buy me lunch and we go for 90 minutes and you get my brain."Those lunch conversations changed everything. Alexandria realized she was more energized talking business strategy than drafting legal documents. Now as founder of Ripples Edge Advisors, she helps business owners prepare for exits before they're forced to sell.Most owners think exit planning means getting financials in order and hoping for the best. Alexandria starts differently. She has clients close their eyes and picture life five years after selling: What does your typical day look like? Who are you spending time with? What gives you purpose?Those answers determine whether you should target private equity (focused on returns) or strategic buyers (who care about legacy and team). The visioning exercise prevents what Alexandria sees constantly: post-exit depression, even among sellers who make life-changing money.Right now she's watching clients in tech-adjacent industries get multiple serious offers in the same week. Legal tech, agricultural tech, climate tech - traditional industries adding technology are hot. But success isn't just about timing the market."If you were to go to Bali for three weeks, would your business run without you?" That's Alexandria's test for exit readiness. Most entrepreneurs think they're prepared until they actually try stepping away.In our conversation, Alexandria breaks down her exit readiness assessment, explains why the visioning exercise matters more than most tactical work, and shares what's driving current M&A activity in her clients' industries.• • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/alexandriaseydel• • •FOR MORE ON ALEXANDRIA SEYDEL LinkedIn: https://www.linkedin.com/in/alexandria-seydel/Company: https://www.linkedin.com/company/ripples-edge-advisors/Website: https://www.ripplesedgeadvisors.com/FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/https://www.coreykupfer.com/Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!

Think investors who don't re-up for your next round are doing you a favor?Not the case!Most entrepreneurs see this as rejection. But here's what Sahil Patel discovered after 11 years building and selling ER Express: Sometimes the BEST thing that can happen is getting misaligned investors out of your cap table.His family office investors knew service businesses. But SaaS? Different game entirely."The way you look at a SaaS business, you really have to look at unit economics. If you just look at the whole cost, it looks terrible."The result? A year of treading water while growth stalled.But here's where it gets interesting: Those same investors offered him a management buyout with seller financing. NON-RECOURSE.Eight quarters of consecutive growth followed.We'll dive deep into this (and so much more) in this episode of the DealQuest Podcast! How to identify when investor misalignment is killing your business Why timing is the entrepreneur's biggest enemy (not money) The crisis pivot that doubled his total addressable market Building performance-based business models that guarantee results And much more Whether you're navigating complex investor relationships or building systems for sustainable growth, this conversation provides frameworks every business leader needs.• • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/sahilpatel• • • FOR MORE ON SAHIL PATELhttps://www.linkedin.com/in/sahilanamipatel/https://www.spiralyze.com/ FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!

JP Morgan's latest M&A report reveals something fascinating: despite ongoing uncertainty, global deal volumes hit $2.2 trillion (up 27% year-over-year).Here's what caught my attention: - Mega deals increased 57% because bigger players can thrive when smaller competitors freeze up. - Cross-border activity actually grew 24% despite rising protectionism as companies use M&A to position around trade uncertainties rather than avoid them. - And get this - AI infrastructure needs will drive $1 trillion in spending over the next 5 years, with data center capacity needing to increase 100-fold.Technology M&A surged 42%, financial services up 56%, and even media jumped 51% as consolidation becomes a survival strategy.The bottom line? Uncertainty isn't going away, but markets remain remarkably resilient. Smart deal-makers are learning to operate effectively in permanently uncertain conditions rather than waiting for clarity that may never come.Listen to my full breakdown on this solo DealQuest episode.• • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/JPMorgan2025• • •FOR MORE ON COREY KUPFER:https://www.linkedin.com/in/coreykupfer/http://coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!

Ever wonder how great dealmakers got their start?Some began with childhood lemonade stands. Others learned through necessity when family circumstances required quick business education. A few discovered their talents through door-to-door sales or car flipping as teenagers.But here's what's fascinating: every successful dealmaker has an origin story that reveals the early development of skills that would later drive millions in transactions.In this best of compilation from the DealQuest Podcast, you'll hear from over a dozen successful business leaders sharing their very first deals - from Thomas Samuelson negotiating his way out of Philadelphia to Sunny Vanderbeck subcontracting lawn care in elementary school.What you'll discover: How childhood businesses teach fundamental negotiation principles Why early sales experiences translate directly to deal success The common patterns that predict future dealmaking ability How adversity often accelerates business skill development And much more Whether you're developing your own deal skills or helping others recognize their potential, these stories provide insights into how business instincts develop and grow. • • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/originstories• • •FOR MORE ON COREY KUPFER:https://www.linkedin.com/in/coreykupfer/http://coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!

Most people think private equity means gutting companies and squeezing margins. Neal Cobb is proving them wrong.After raising over $20 million and scaling his delivery startup to 100,000 drivers before selling to 7-Eleven, Neal could have retired. Instead, he's building something that challenges everything we think we know about private equity.At Equity X, they're acquiring legacy businesses and turning them into employee-owned enterprises. No quick flips. No cultural destruction. Just long-term value creation where employees actually benefit from the success they help create.In this DealQuest conversation, Neal shares how he went from running dice games in high school to building a white-label delivery empire to reimagining what private equity can be. His insights on partnerships, timing deals, and betting on people over ideas will change how you think about business growth.Neal's approach reveals what happens when you prioritize people and culture alongside profits.This is a perfect listen for business leaders exploring acquisition strategies and sustainable growth models.• • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/nealcobb• • • FOR MORE ON NEAL COBBhttps://www.linkedin.com/in/neal-cobb-4a4084179/www.equityx.co FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!

 Eighty percent of business owners have eighty percent of their net worth locked in their business.But only twenty percent of businesses survive to see their tenth birthday.This conversation will change how you think about building enterprise value forever.Scott Beebe didn't just build a successful consulting practice...He proved that the secret to enterprise value isn't your product, your market, or your marketing.Scott is the founder of Business on Purpose and certified exit planning advisor who has helped hundreds of business owners liberate themselves from chaos while building sellable assets.In this DealQuest Podcast episode, I sat down with Scott to uncover the real drivers of enterprise value and why most businesses fail the ultimate test.In our conversation, we explored: The eighty percent rule that destroys most businesses Why your product isn't actually your product The enterprise value litmus test every owner should know How to break free from "hero complex" that kills scalability The five meeting types that build culture and systems Cash domination strategies that put owners in control And much more!Whether you're planning an exit in two to three years, building for long-term growth, or struggling with operational chaos, this conversation provides actionable frameworks for immediate implementation.  • • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/scottbeebe• • • FOR MORE ON SCOTT BEEBECompany: https://www.businessonpurpose.com Assessment Tool: https://www.businessonpurpose.com/healthy Books: "Let Your Business Burn" and "The Chaos Free Contractor" FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!

Most business leaders believe they need significant capital to pursue growth deals.This assumption limits their strategic options.The reality is that dozens of deal structures are available to businesses of every size, yet most entrepreneurs only explore a fraction of what's possible.From acqui-hires that appear to be acquisitions but are actually strategic hiring initiatives, to licensing agreements that generate ongoing revenue, to joint ventures that create value for all parties involved.This episode of the DealQuest Podcast explores the full spectrum of deal opportunities:• The crucial distinction between mergers and acquisitions and why it matters for your strategy • How to structure transactions with zero upfront capital requirements • Why licensing represents the most underutilized revenue opportunity for many businesses • Employee retention strategies that function as internal deals • And much moreEssential listening for business owners seeking to understand their complete range of strategic growth options.• • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/languageofdeals• • •FOR MORE ON COREY KUPFER:https://www.linkedin.com/in/coreykupfer/http://coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!